Regiospecific conversion of oxiranes, oxetanes, and lactones into difunctional nitrogen compounds via aminosilanes and aminostannanes
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2261-2265
- https://doi.org/10.1039/p19840002261
Abstract
The insertion reactions of diethylaminotrimethylsilane (TMSDEA) and diethylaminotrimethylstannane (TMSnDEA) into oxirane, oxetane, and lactone rings are reported. Regioisomerically pure β- and γ-amino alcohols were obtained, with AlCl3 or Et2AlCl catalysis, from monoalkyloxiranes and monoalkyl-and aryl-oxetanes respectively, whereas, in the majority of cases, reactions involving polysubstituted oxiranes resulted in a loss of regioselectivity. Ring-opening reactions of the lactone rings with TMSDEA led, on the other hand, to β-amino acids or to ω-hydroxyamides depending upon the ring size. With TMSnDEA, spontaneous ring cleavage of the alkyloxiranes and of β-propiolactone occurred with reversed regioselectivity, while the oxetanes and γ- and δ-lactones were opened with the same regiochemistry as that found with TMSDEA for the same ring systems.This publication has 0 references indexed in Scilit: